‘Help! I Suck at First Dates’

Illustration: Pedro Nekoi

This column first ran in John Paul Brammer’s Hola Papi newsletter, which you can subscribe to on Substack.

¡Hola, Papi!

I’m a 20-something straight guy (audible booing) who’s not very good at first dates (booing intensifies). Maybe it’s nerves, maybe it’s that I’m a deeply uninteresting person who lacks life-changing trips abroad or near-death experiences to talk about, but whatever it is, I just feel like I have all the personality of a dead fish the second I sit down across from a lovely lady at the restaurant where we agreed to meet.

To be honest with you, watching myself fail to enchant yet another woman on these dates makes me feel like a complete incel. It’s a little pathetic. I do think it comes down to my lack of charisma (I’m rizz-less, as the kids would say), as I feel I’m decently attractive and I typically don’t struggle to find a date in the first place. 

Papi, is there something I’m missing here? Some secret trick to leveling up my conversation game? Or do I need to accept that I’m as charming as an eel? 

Wet Paper Bag

Hey there, WPB!

I find eels to be incredibly charismatic. I remember early in the pandemic when that Japanese aquarium invited people to FaceTime with their eels because they were forgetting what human faces looked like. I checked in with them all the time, though there was often quite the queue. This is to say, there’s actually a chance you are less charming than an eel. Eels have no issue getting people interested in them.

It’s wonderful to see that I’m getting letters from straight men. It’s truly the final frontier for this column, which has found resonance among gay men, straight women, and lesbians who watch anime. Go tell all your buddies that ¡Hola Papi! is a safe environment where we accept clicks and metrics from all walks of life, even exotic ones such as yours.

As for your conundrum, I totally get it. First dates are a veritable playground for insecurities, and it’s incredibly easy to get in your own head about it. This is especially the case nowadays, since we tend to get our dates from apps, where we haven’t yet tested any in-person connection whatsoever. You never really know who’s going to walk through that door and give you an awkward little hug. It’s kind of scary! It’s understandable to be anxious about it.

But I did notice some things in your letter that make me feel like we can locate a few areas for improvement, the term lovely lady among them, though I’ll politely ignore that one, because I don’t have any good reasons for reacting the way I did. This could be my own prejudices seeping in, but “lovely lady” sounds like the kind of thing a man with dozens of Funko Pops would say. Not that there’s anything wrong with that. Love is love.

For starters, it’s important to remember that you’re on a date in the first place to check your chemistry with another person. There’s a decent possibility you will not have any. A dry conversation, though unpleasant, is an indicator that it’s not a match. That’s the purpose of a first date, fulfilled.

But that doesn’t mean there aren’t other factors at play, and you’re absolutely right that we can get in our own way when it comes to carrying a conversation with another person. I notice in your letter that you’re focusing on your own performance quite a bit. You’re watching yourself! That can lead to getting in your own head too much and being awkward. We don’t want that. We want to be cool.

The thing about being cool is, you don’t need to have gone on life-changing trips or had any near-death experiences to achieve it. Honestly, on a first date, if someone is trying too hard to be interesting, it’s kind of a downer. I think a good first date is one where both parties make an earnest attempt to get to know each other, and that involves a lot of listening.

There are people who will give you great “first-date questions,” and those can be useful, but I find that first dates are more about responding to the energy of the moment. Good first-date questions, in my experience, are follow-up questions. When she tells you where she’s from, what she does, the things she likes, the best questions are ones that show you’re listening and interested in going deeper. What was that like for you? What got you interested in that? And so on.

A good conversation isn’t one in which we’re simply waiting to speak. It’s one in which we find mutual interests that we can go back and forth with. Sometimes, this is arduous, yes, and sometimes the conversation is so basic it starts to feel like a worksheet from a Spanish-language textbook: What is your favorite color? Do you like the fiesta? Where is the discotheque?

It happens! But first dates are a great time to practice confidence, which is a noun, but actually something you do. I like to tell myself “I want to get to know this person” before a date, setting a productive intention that’s a lot less scary than “I want to make this person like me” or “I want to impress this person.”

Other people are just as complex as we are, WPB. They might be nervous too! There’s nothing to be intimidated by. Try to enjoy each other’s company and have a good time.

Con mucho amor,

Originally published on March 7, 2024.

Purchase JP Brammer’s book Hola Papi: How to Come Out in a Walmart Parking Lot and Other Life Lessons here.

‘Help! I Suck at First Dates’